Decoding Value in the Digital Learning Space

In our constantly evolving world, the need to upskill and reskill the workforce has become more pressing than ever, especially in the healthcare industry that is grappling with the impact of COVID-19. To address this challenge, several startups have emerged in the digital learning space, providing learning-based solutions to healthcare, among other industries. While the […]

How Emphasizing "No" Over "Yes" Can Shape Your Investment Success

Are you a capital allocator who understands the true power of saying “no” in the investment world? Discover the art of declining investment opportunities and the profound impact it can have on your lo As a capital allocator, we place more emphasis on saying “no” than “yes”. Sometimes, declining an investment opportunity can be challenging. […]

SaaS Landscape Observations in 2023

Let’s talk SaaS. In this current startup climate, we’ve got two competing forces: a shrinking economy and an outdated B2B sales approach. Not exactly ideal, right? This brings me to a tweet I love by Harry Stebbings (above). So, what’s the game plan? First things first, figure out if your company has what it takes […]

Over-Rotating on Short-Term Fake Signals.

Starting a business is never easy, especially in the early stages. As a founder or venture capitalist, it can be tempting to chase after every potential opportunity that comes your way. However, this can ultimately lead to over-rotating on certain decisions and losing sight of your initial goals and objectives. One key area where this […]

Hype Cycles IRL

During my run today, I noticed two Waymo cars parked in the neighborhood. As you may know, the company is launching a driverless ride service. This got me thinking about the major tech players in the autonomous car market, including Google (Waymo), Apple, and Tesla. I’ve often wondered why there’s a rush to this technology. […]

You Can't Be Open Minded Enough in This Investing Environment

I had lunch with the commercial real-estate king of Arizona yesterday and we were talking about all the things going on in the world – interest rates, regional banks, work from home etc. I asked him what he saw in the tea leaves for the future of commercial real-estate. He told me “In my 40-years […]

The Illusion of Being the Smartest Person in the Room

Have you ever had that feeling that you are the smartest person among your peers? Or maybe you think that you know everything there is to know about a particular topic? It is a common trait among people, but what if I told you that this way of thinking is just an illusion? The truth […]

The Pendulum of Platforms vs. Best-in-Class Software Solutions

As technology continues to shape and change our lives, we experience an ever-changing market of software solutions. At times, the market swings towards platforms, which bundle all features together and make them available as a single offering. At other times, it swings towards best-in-class solutions, where each feature is available individually and provided by a […]

Its Monday LFG ?…and What It Takes to Be a Generational Investor

Its Monday everybody LFG! ??? As I spend my last couple of weeks in Phoenix before leaving for Carlsbad, there’s an endless list of errands to run; from dental and medical appointments to limited partner meetings and what not. Despite closing a deal in January I feel a little behind in my deal sourcing for […]

#1 Killer Question: If I Was to Give You $10M to Invest…

Allocating capital into startups is one of the most challenging and exciting things you can do as an investor. As a generalist investor, the challenge is especially hard. You are a functional expert in nothing, making it hard to identify the next big thing. Being a vertical saas investor makes this even more difficult. As […]

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I get up early, like really early—truly, at an unfathomable hour. As part of my morning ritual, I engage in expressive writing to bring clarity to the labyrinth of my thoughts. Delving into topics encompassing startups, investing, and personal growth. People seem to like it.